Growing up in the rough neighborhoods of 1915 New York, Nathan’s only skill was the con. A true innovator, Nathan learned from some of the quickest confidence men on the streets, and by the time he was 20, he was making up cons of his own. Nathan’s ego thrived on pushing buttons and he became so skilled he could gain the trust of a nun if he wanted to.

Nathan was good. He could rob you so fast that if you blinked, you’d miss the whole thing. But one night, Nathan made a powerful enemy with a well-known gangster by the name of Louis Kushner when he lifted Louis’ gold watch at the local pizza joint. Nathan got away, but Louis swore he would get him back.

Nathan heard his warning, but couldn’t help pushing Louis’s limits. One day, he pushed too far by going after his little brother, Charlie. Nathan came up with something he called a Drop Swindle, based on gaining the trust of an honest mark to exploit their morality and take advantage of their sympathy.

The Drop Swindle consisted of several counterfeit hundred-dollar bills stuffed into a wallet and a slow-witted mark. The mark and the conman ‘find’ the ‘dropped’ wallet at the same time. Explaining he is in a rush and has somewhere he’s supposed to be, the conman agrees to ‘let’ the mark return the wallet for an anticipated reward if the mark will compensate him with a finder’s fee. The conman then disappears while the mark is rewarded with the fake bills. Nathan’s Drop Swindle worked like a charm on Charlie.

This time Nathan’s drop wasn’t fast enough. The con had gained the attention of Louis, when the money Charlie handed over was the protection money he had just collected on Louis’ behalf.

In the summer of 1923, police found Nathan’s body bruised, bloodied and riddled with bullets, crumpled in the corner of an alley. Turns out Louis Kushner finally got the drop on Nathan “Kid Dropper” Kaplan.

The Spanish Prisoner is a classic long con that gained popularity back in the late 1930’s. A sometimes complex and layered con, The Spanish Prisoner became the basis for David Mamet’s 1997 suspense thriller of the same name. Steve Martin plays the role of a successful businessman offering to ‘help’ an unsuspecting ‘mark’, but instead roping him into an elaborate con that nearly robs him of everything, including his life.

The film’s ‘mark’, Joe Ross (Campbell Scott) invents a lucrative industrial process that has not been patented. While at an island resort, Joe befriends Martin’s character Jimmy Dell and his new secretary Susan Ricci (Rebecca Pidgeon). Seeing that he is single, Jimmy wants to introduce Joe to his sister and asks him to deliver a package to her. Out of suspicion Joe opens the package on the plane, and finds it’s just a book about tennis, but accidently rips the cover. He buys and delivers a new book.

As a thank you for delivering the book, Jimmy takes Joe out to dinner at a club, but before entering, Jimmy has Joe sign a certificate so that he can become a member of the club too. Jimmy reveals that he has opened a Swiss bank account for Joe with some money it in as an additional thank you. Jimmy goes on to suggest that Joe’s company and his boss, Mr. Klein might not give him fair compensation for his work, but Susan tells Joe to trust no one. Joe learns that the sister is a ruse and that Jimmy is actually a confidence man attempting to steal his work. Joe contacts the FBI agent he met on the island and is enlisted in a sting operation. To his horror, Joe learns that the agent is actually part of Jimmy’s con, his process is stolen and he is left with nothing.

Joe goes to the police, who think his story is far-fetched. The con has made it appear that Joe sold his process to the Japanese, the Swiss bank account makes it look like he is hiding assets, and the form he signed to join the club turns out to actually be a request for political asylum in Venezuela, which has no extradition treaty with United States. The police also show Joe that Jimmy’s apartment and the club don’t exist - they are just rooms at the back of a restaurant. None of this looks good on Joe. To top it off, Joe has been framed for the murder of his co-developer of the process.

Now on the run from the law, Joe reconnects with Susan who believes his story and expresses a romantic interest in him. Joe remembers that the hotel on the resort has video surveillance, which could prove that Jimmy Dell was there. Susan accompanies Joe back to the island, but she too turns out to be involved in this elaborate con. At the airport, the ‘camera bag’ Susan gives Joe actually contains a gun and an airplane ticket to Venezuela. Before passing through security, Joe realizes what is happening and, without letting Susan know he’s onto her, bolts for the door with Susan in tow.

Joe leaves the airport with Susan and boards a ferry to return home. Jimmy comes to kill Joe on the ferry, which holds only Susan and Japanese tourists. As Jimmy moves in to finish Joe off, he is hit with a tranquilizer dart shot by one of the tourists, who are in fact US Marshals who have been monitoring the con since the beginning. While Jimmy and Susan are taken off to jail, the Marshals reveal to Joe that his boss, Mr. Klein, was behind the entire con and wanted to keep the process and all the profits for himself,

The Mamet version of this con is elaborate and layered, but is nevertheless reflective of the brilliance of the insight into human psychology and behavior that makes it possible to achieve. This incredible forethought is what sets The Spanish Prisoner apart and makes it a classic. Always remember, if what you’re giving away is more important than what you might get back, you’d better hold on tight.

In the winter of 1952 Korean War Vet, Reggie Tomkins, best known to his fellow vets as ‘Cyclops’ used a con that took advantage of the very handicap that got him sent home from the war: his smooth glass eye.

After an honorable discharge stole Reggie’s “best years and best eye”, work was harder to find in his hometown of Illinois than a cobra in Alaska. Reggie was turned down everywhere he went and his disability fund was dwindling fast.

Reggie decided to pick up and head out to Chicago in search of new opportunities and ran into old army buddy, Karl Johnson. Karl was a greedy old fool who needed some extra dough in a bad way. He proposed to Reggie that together they could take all the bars in Chicago, one at a time without lifting a finger and they’d both be set for retirement.

Karl and Reggie worked as a duo, relying on their old age and ex-vet status to evoke patriotism and compassion for a war hero. Reggie would come in to a bar and begin chatting up the regulars, reciting old war tales and eventually getting around to how he lost his eye and the bountiful disability payments he was receiving as a result. Before the night was out he would announce to the bar that in his drunken stupor, he somehow lost his trusty glass eye, and would go on to offer a $1000 reward for anyone who found it. He would leave a phony number and address and disappear into the night. Karl would walk in shortly after Reggie’s exit and while the regulars searched for a non-existent eyeball, Karl would claim to have found it, without knowing much about what it even was. Inevitably, someone who had heard Reggie boast about his disability payments and wanted the bulk of that reward for themselves would offer Karl a small portion of the $1000 reward with the plan to return the eyeball themselves and collect the full bounty. Karl would take no less than $250, and would walk out with effortless cash in hand.

Karl and Reggie, became known as the "The One-Eyed Bandits" hit about 30 bars a month across 5 different states and managed to rake in a cool $2,687,500, minus a few hundred for fake eyeballs.

Born in 1871 in the Texas panhandle to a clockmaker and teacher, William Radley was orphaned at age 3 and spent his formative years with an uncle who ran a traveling medicine show. He grew up and into the role of Tip Man, the character who would gather a crowd when the show pulled into a new town. Jawing with anyone and everyone, William developed his skill as a talker to the point that he could captivate the attention of whoever he liked.

He was also an excellent pickpocket, but he was small potatoes until the day in New York City that he walked up on a group and saw Howard Thurston doing street magic for amazed passersby.

Thurston
had not yet made his name, but was gaining a reputation as an innovator in the
craft. Radley was amazed by the incredible array of misdirects Thurston was
using to capture the audience�s attention and move it wherever he wanted it to
go. Ultimately through his mastery over their focus, he was able to deliver to
them an indelible experience.

Radley quickly realized that combining the dexterity of his finely tuned fingers, or 'digits', with the attention capturing spectacle of Howard Thurston's magic, might be a way into a much much larger idea - one he would come to name in honor of its muse. And so the Digital Howard was born.

The Digital Howard relied upon creating a public distraction in order to capture the attention of as large a group of people as possible, and then to unobtrusively relieve them of their valuables. Performing his amateur street magic on a busy sidewalk, Radley would subtly pickpocket one member of the audience, and then plant the stolen item in the pocket of another audience member. He would then enlist that same person in his next trick, asking them to turn out their pockets as part of the routine. When the stolen item was displayed and recognized by its owner, inevitably a fight would start between the two parties, the crowd would grow and, as the argument heated up, Radley would slip out and make his way through the crowd, fleecing pockets the entire way. His largest take was 323 people at one time.

If therewas one thing the early 1900’s gave us, it was great music. Bennie Moten was a struggling musician who wanted to make something everyone could jive to, but inspiration didn’t come easy in the poor neighborhoods of St Louis. Even worse, Bennie’s little sister, Carla, had an awful infection that was getting worse by the day and he didn’t have a dime to give her for medication.

Carla had a teenage son named Julius, who spent his days loitering in the streets and playing hooky from school. It wasn’t until one night when he saw his mother in really bad shape, that Julius knew he had to get her that medication. Julius knew exactly where money came from and went straight to the source, Joseph and Peter DiGiovanni

The brothers had arrived in Kansas City from Sicily in 1912 and ran things there. They were enough of a presence around town that Julius was familiar with them and the way they ‘did business’. Julius went to Peter DiGiovanni and asked if there were any problems that needed fixing - anything that he could help take care of to earn some cash. DiGiovanni, thinking that Julius was nothing more than an inept little kid, jokingly told Julius that the only thing he needed to take care was Kansas City police detective Louis Olivero, a bristly, paranoid old cop with a mean streak, who had been investigating The DiGiovanni’s for extortion. Olivero was becoming a nuisance and the DiGiovannis had had enough of him.

DiGiovanni laughingly offered Julius a thousand bucks if he ever managed to kill Louis Olivero, and Julius eagerly accepted, asking what Olivero looked like and where he could be found. Julius headed over to Olivero’s favorite bar and intentionally bumped into him. Olivero was incensed, and yelled at Julius, and Julius calmly offered to buy him a drink to apologize. Julius brought back a beer and a coke, and very subtly poured something into the beer while Olivero was distracted. One of Olivero’s buddies spotted this and quietly ratted the kid out. Olivero had suspected the kid was sent by DiGiovanni and decided to take care of the matter himself. Wrapping a burly arm around Julius, Olivero offers to trade drinks, announcing that since the kid had never had beer before, this would be a great way to start. Julius reluctantly agrees and slowly takes a sip of the beer. Olivero forces him to down the rest, while he sips on Julius’ coke.

By the end of the night, a drunken Julius informed DiGiovanni that all his troubles would be over starting tomorrow. Sure enough, headlines the next day trumpeted the death of Louis Olivero. Although the cause was listed as murder, with Olivero having been shot in the back, it was clearly spin, because none of the Kansas City police would let the public story be that one of their own was taken down by a little kid. As DiGiovanni handed over an envelope with a thousand dollars in it, Julius explained that he used Olivero’s paranoia to finish him off. Julius had already poisoned his own coke at the bar and what he put in Olivero’s beer was just regular old sugar.

Word of Julius’ scheme spread and when Julius came home with a months worth of medication for his mother, Bennie knew that the rumors of Julius outsmarting Louis Olivero were true. Bennie was so impressed at the kid’s ingenuity, inspiration struck and he wrote a catchy new jazz tune called the ‘Kansas City Shuffle’, named after the classic scheme that Julius employed to take out Egan. The song caught the attention of a recording agent who put Bennie on tour, launching his career and forever enshrining Julius in popular song.